


Hell in Heels

by Lil_Lizard_Leah



Category: IT (2017), IT (Movies - Muschietti), IT - Stephen King
Genre: Anal Fingering, BDSM, Dom/sub, Fluff and Smut, High Heels, Improper Use Of Stilettos And Finger Condoms, Lingerie, M/M, Object Insertion, Smut, Stiletto Heels
Language: English
Status: Completed
Published: 2020-01-19
Updated: 2020-01-19
Packaged: 2021-02-27 13:34:08
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,662
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22258030
Author URL: https://archiveofourown.org/users/Lil_Lizard_Leah/pseuds/Lil_Lizard_Leah
Summary: Since they've begun dating, Stan and Bill have become quite the adventurous couple in the bedroom. There's not much they haven't tried, so when Stan picks up a new present for them to use in unconventional ways, Bill can't help but be intrigued.
Relationships: Bill Denbrough/Stanley Uris
Comments: 3
Kudos: 41





	Hell in Heels

It was 5:53 on a Friday evening; an unopened box of pizza sat on the kitchen counter, awaiting the arrival of its second eater. Bill was lying in bed, scrolling aimlessly on his phone, trying to pass the time between every anxious glance up at the clock. As per usual, he’d arrived home from work an hour before his boyfriend. He’d wasted no time in ordering them a pizza for dinner, and then shucking off his stiff work clothes as soon as it had gotten delivered. That hour at home alone was by far his least favorite part of every day, but today was even worse, because today he had to wait _two_.

Stan had texted him earlier in the day and told him he’d be home late. Bill knew he was being a brat for being upset about something as trivial as one hour. Two of his best friends were in a long-distance relationship, and they often went months without seeing one another. But Bill couldn’t help that he’d gotten attached to the consistency at which he got to marvel in Stan’s soft kisses and gentle touches, couldn’t help that he felt empty when they’d spend even an extra hour apart.

The sound of the front door opening pulled Bill out of his thoughts, and his feet were carrying him into the living room before his brain had even caught up. He barreled into a tall frame, not even bothering to say hello before peppering kisses along Stan’s neck.

Stan chuckled above him, dropping his belongings to the floor with an unceremonious clunk before curling his arms around Bill’s frame.

“Miss me?” Stan teased.

Bill grumbled something incomprehensible into the fabric of Stan’s shirt, earning another laugh.

When he finally separated himself from his boyfriend’s arms, Bill noticed a big box accompanying Stan’s messenger bag.

“What’s th-that?” Bill nodded in the direction of the mystery item.

Stan’s eyes lit up behind a small smirk. He let himself take in his boyfriend for the first time since walking through the door. Bill’s hair was a mess from laying in bed for the past couple hours, the quickly fading indentation on his cheek from his pillow another indication. But what really drew Stan’s attention was the pair of black boxer briefs that cut through the expanse of creamy skin. Stan quirked an eyebrow at Bill in question.

“It’s w-warm in our apartment.” Bill shrugged, looking slightly abashed at the reaction his attire had garnered him.

Stan decided it was better that Bill was already undressed, considering what he had planned for them tonight.

Stan placed his hands on either side of Bill’s face, pulling him in for an unexpected slow kiss.

“Not that I don’t l-love this,” Bill said between kisses. “but are y-y-you going to sh-show me what’s in the b-box?” Stan smiled against Bill’s lips before pulling away.

“Go wait in our room.” Stan turned Bill around by his shoulders and slapped his ass, pushing him in the direction of their bedroom. Bill yelped in surprise before dissolving into giggles as he disappeared down the hall.

It didn’t take long before Bill started to get impatient. He was sitting on the edge of their bed, picking at a thread on their duvet cover when he finally heard something from the other room. He couldn’t place the sound right away, but the steadiness of the clicks got louder as Stan approached the room, and Bill’s mind pieced things together just as Stan strode through the doorway.

Stan’s demeanor was completely casual. He walked with his usual air of confidence, even with the five-inch death spikes he now wore on his feet.

Despite them being intimidating, Bill couldn’t deny they were incredibly sexy. He watched as Stan stopped in front of their full-length mirror to admire himself, as if Bill wasn’t even in the room.

The heels were sleek; slender red numbers with a considerable heel attached. They poked out just the right amount beneath the cuff of his work pants. Bill followed the length of Stan’s legs, now somehow impossibly longer than they already were, and settled his attention on the crimson stilettos. 

“Those are n-nice.” Bill commented, adams apple bobbing in his throat as he swallowed down his budding arousal.

Stan turned slightly to admire a different angle in the mirror, cocking his hip to accentuate the curve of his ass. His suits were tailor made for his body, with clean lines and sharp creases to make him look as presentable as possible, and if you asked Bill, as _fuckable_ as possible. In combination with the new additions, it made Stan godly in Bill's eyes.

“They are, aren’t they?” Stan responded coyly.

Bill’s response was exactly what Stan had been hoping for, but with what he had planned, he needed Bill just a little more pliant.

Ignoring Bill’s reflection in the mirror, Stan kept his eyes on his own reflection as he began unbuttoning his shirt, taking it off along with his suit jacket and moving to fold them over the back of his desk chair.

He heard the hitch in Bill’s voice when he noticed the garter belt attached around Stan’s waist, disappearing into the waistband of his dark slacks. Stan pretended not to notice, spending extra time undoing his pants just to leave Bill waiting. When he couldn’t draw on the process any longer, he bent at the waist as he pulled his pants down, exposing white flesh and red lace and black nylon all at once.

He stepped out of his pants and straightened himself, adding them to the neat pile of clothes on his chair. He turned to face Bill, hiding his knowing smirk under a facade of innocence as he approached his boyfriend.

“Y-y-you were wearing those a-all day?” Bill gulped, eyes unabashedly raking up and down Stan’s form.

Stan looked down at himself, eyeing his sheer black thigh highs held up by thin garters that only worked to frame the way his cock was barely contained in the red lace panties he wore. Red, just like the heels he bought. Just like the marks that littered his frame from their morning activities.

“Mhm.” Stan nodded, reveling in the way Bill’s pupils dilated at the thought.

Stan closed the distance between them, placing his knee into the spot between Bill’s legs and pushing them both down on to the mattress. His arms came up on either side of Bill’s head, caging him in, locking his gaze, teasing him with just the slightest bit of pressure from his knee.

“I was thinking of you all day.” Stan whispered in Bill’s ear as Bill’s warm hands gripped onto his sides. “I was thinking of you when I bought them.”

It took a moment for Bill to come out of his daze and realize Stan was talking about the heels.

“M-me?” Bill questioned, a flush spreading down his chest.

“Yeah. I was thinking about how much fun we could have with them.”

Stan’s devilishly sinful grin told Bill everything he needed to know, his cock already twitching at all the possibilities running through his head. Bill pulled Stan down into a feverish kiss, his grip tightening around Stan’s waist to pull him flush against his chest.

The kiss grew heavier as the minutes ticked on, the eagerness heavy in the air above them. Stan’s hands explored the planes of Bill’s body, feather light touches that left goosebumps in their wake. When he reached Bill’s abdomen, he could already feel the anticipatory tensing of his muscles.

Stan broke the kiss only to move his lips down Bill’s neck, stopping at the dip in his collarbone that always riled him up. Stan sucked on the fading bite mark there, giving it new life as red and purple splotches rose to the surface under his tongue. Bill’s moans could be heard among the gentle city bustle filtering in through their window, a symphony that Stan would sear into his memory.

Stan moved down Bill’s body, teeth grazing tender flesh on the way, until he hit the waistband of Bill’s briefs. The thin material wasn’t doing Bill many favors at hiding his growing need, the cotton spread taught over the impressive tent. Stan made eye contact with Bill, who was watching intently with lidded eyes, before mouthing at his cock through the briefs.

Stan felt the small thump on the bed as Bill threw his head back, whimper escaping his bitten red lips. Stan wanted to hear it again and again, continuing his teasing for a maliciously long time before he finally took pity on Bill’s hoarse voice and begging pleas.

“More… S-Stan… please… _HNNNGG_ -” Bill’s pleading was cut off as Stan pulled his boxers down and got his mouth on him in one swift movement. Bill felt heavy on his tongue, his cock having grown to full hardness under Stan’s teasing. Bill was a considerable length, hard to swallow down fully unless Stan really concentrated, but his girth was what really made Stan’s jaw protest. So instead, Stan swirled his tongue around Bill’s head, leaving small kitten licks up his frenulum and tracing the veins on the underside of his cock.

“Did you clean yourself out today?” Stan asked between licks, already going over his plan in his head.

Bill nodded above him, too busy writhing on the bed to give him a proper answer.

Stan stopped his movements altogether, letting Bill’s cock fall against his stomach with a wet slap.

“W-wh-”

“Use your words. I asked you a question.”

Bill stared back at him, mouth gaping around his words.

“Y-Yes…” 

“Good boy.” Stan smiled, leaning up to peck a still reeling Bill on the lips. “Hands and knees.” He ordered softly, enjoying the way Bill scrambled to flip himself over as quickly as possible, clearly excited about what was to come.

Stan took a moment to gather what he needed from their toy chest. It was a big wooden piece that passed as decor to the unseeing eye, but once it was opened, it held all the lewd treasures one could imagine. Once he'd procured lube and toy cleaner, Stan was back on the bed, rubbing a soothing hand along Bill’s back.

“What’s your color, baby?” Stan whispered while he stationed himself behind Bill, his hands now kneading Bill's cheeks apart.

“Green.” Bill confirmed, pushing back into Stan’s grasp.

With that, Stan popped open the lube and squirted a generous amount on his finger. When he brought it up to the awaiting ring of muscle he watched as Bill’s hole fluttered under his touch. Stan _tsked,_ circling the pucker.

“Already so desperate for me…”

When his finger finally slipped in Bill responded with a full body shiver and a breathy sigh, his tension visibly releasing.

“There we go baby, relax yourself for me.” Stan cooed, running his free hand down Bill’s spine soothingly.

Stan continued to finger Bill slowly, crooking his index to graze that bundle of nerves that had Bill humming with pleasure. He kept going until Bill was loose enough that Stan could fit another finger in, but instead of doing so, he pulled his hand away and began prepping his surprise.

Stan first used the toy cleaner to sanitize, spraying it a few inches away from the heel of his stiletto and then wiping it away with a paper towel a few moments later. The heel would be covered anyway, but Stan was nothing if not prudent. He didn’t want any tears in the condom to result in Bill having dirt up his ass, that would _probably_ ruin the moment.

Another clever way Stan had figured out to decrease the possibility of tearing was to use a finger condom rather than a regular one. They were much smaller, and therefore wouldn’t result in as much latex rubbing against itself. Stan and Bill had bought a pack of finger condoms a couple years ago when they’d just begun exploring each other, and Stan had still been unsure about cleanliness.

After checking the expiration date on the package, Stan proceeded to unwrap one and roll it up the heel. After seeing how it flopped back down, uncooperative and still slightly too large to stay up on its own, Stan checked their bedside drawer for something to help secure it in place. After some rustling around, he found a small clear elastic that had no doubt belonged to Beverly, ended up on their floor, and gotten thrown into the drawer out of laziness. But he’d still thank the gods above _and_ Beverly for this gift.

After wrapping the small elastic around the very top of the condom, holding it up but making sure it didn’t pull too much, Stan turned back to Bill.

Bill was buzzing with excitement, having put together the (very obvious) clues and figured out what was in store for him. They had never experimented with something like this, but he knew that Stan would never put him in any danger, and if this was something that Stan was initiating, it was because he’d done thorough research on it. So Bill stayed relaxed, in a daze of affection as he watched his boyfriend prepare for this new experience.

“Come here.” Stan patted the end of the bed, ushering Bill to lay on his stomach and scooch down the length of the mattress until his lower half was hanging off, balanced on his tiptoes.

“Spread your cheeks for me, pretty boy.” Stan whispered gruffly.

Bill did as he was told, reaching back with both hands and pulling his cheeks apart. It was an intoxicating view, his hole was puckering its lips at Stan tauntingly, and Stan couldn’t do it a disservice any long. He needed to spread it wide open.

With an act of bravery and surprising balance, Stan lifted one foot off the ground and placed it directly on Bill’s tailbone, causing the heel of his stiletto to line up almost perfectly with Bill’s awaiting hole. It was a bit hard to keep himself from toppling over without putting too much pressure on Bill’s body, so as a second thought Stan reached out and grasped the bed posts, using them to keep himself stabilized.

With a steadying breath, Stan began rubbing the tip of his stiletto around Bill’s hole, coating the condom with a generous coating of lube that was left over from when Stan fingered him. That alone had Bill crooning.

It was when Stan finally entered Bill, slow and steady, that Bill let a loud moan fill the room. All of the pent up anticipation came gurgling out of him, raw and wanton. Bill tried to push back into Stan but he held him firmly in place with the sole of his shoe, stopping Bill from getting what he wanted. Stan knew how he wanted this to go; slow and torturous, his favorite way to tease.

“How does it feel, baby?” Stan asked.

“Weird. _Amazing_.”

Stan’s lips quirked into a half smile.

“Describe it for me.”

Stan began leisurely fucking his heel in and out of Bill, keeping the movements shallow, leaving Bill straining for stimulation as he tried to describe the feeling.

“It feels… t-t-tantalizing. I almost f-feel empty, but then every time you graze - _hnnnng_ -”

Stan smirked as he watched Bill’s back tense.

“Yeah, _there_ . It’s k-k-kind of like I’m- _aaaaaaahhhh_ \- unp-p-prepared for it, but that just makes it more s-sensitive.”

Stan nodded, though Bill couldn’t see him, his face long ago lost to the sheets below it.

When Stan had thought of this idea, he hadn't been sure what exactly it would feel like. He knew the heel of a stiletto was too thin to give any real resemblance of a cock, but if he angled it just right, he thought maybe it would cause sensations Bill had never felt before. In a way, he’d been right, and seeing Bill’s hole cling to his heel was enough to make the whole thing worth it. What a sight.

But however pretty the view, Stan knew Bill couldn’t cum just from this.

“How’s your pretty cock doing?” Stan asked, already knowing the answer. He could see how red it had gotten, rubied at the tip and an angry fade along the shaft. The only friction it was getting at the moment was occasional rutting up against the bed.

Bill let out a mewl in response.

“Feeling kinda neglected, huh?”

Bill nodded frantically, once again trying to move farther back and get the heel as deep into himself as possible. Stan held strong, using the strength in his thighs (thank you baseball) to keep his wriggly boy in check.

“Yes!” Bill sobbed out after being denied any movement.

“Do you want to touch it?” Stan asked calmly.

“Yes.” Bill sobbed again, this time much quieter and almost defeated.

“Alright baby, I’ll let you touch yourself, _but_ if you can’t make yourself cum in three minutes, you’re not allowed to touch yourself for another thirty.”

Bill’s eyes widened, the challenge leaving his mouth dry and his palms sweaty. The thought of being teased for another 30 minutes with no alleviation made him shudder, so… he’d just have to do it in three.

“O-o-okay.” Bill agreed, looking over his shoulder to send Stan a reassuring smile that he was still on board, Stan could continue.

“I’ll be keeping track of your time.” Stan warned, raising his eye level to that of the clock on their bedside table. He waited a few seconds for it to level out to a number he could easily keep track of, and then he was giving Bill the go.

Bill’s hand instantly shot down to his cock, nearly vibrating under the overdue touch. His other hand led up to his chest, tweaking one nipple and then the other. Before they’d gotten together, Bill had always thought it was a myth that people could get turned on just by having their nipples played with, but Stan had taught him otherwise and _boy_ did he learn fast.

Both of his hands worked in tandem, pulling and squeezing, leading Bill to filthy moans and withering cries, in a desperate attempt to get himself to cum.

A minute had gone by. Steeling himself and using leverage from the bed posts, Stan doubled his tempo. The result was instant; a tightening of muscles, a deep howl, and Bill’s own hands sped up to match the pace Stan set.

He couldn’t be certain, but from Bill’s reactions Stan believed he’d found the perfect angle to rub against his prostate. He made sure to be gentle, given that the heel of a stiletto wasn’t exactly forgiving. He’d made sure when picking out the pair that there were no sharp corners or angles on the heel, but it was still _a heel_ , not exactly something made to be stirring around someone’s insides.

“A minute and thirty seconds to go.” Stan singsonged as they reached the halfway mark.

He paid close attention to how Bill stroked his cock, quick broad jerks where he passed his enclosed fist over the head to spread his precum down his shaft. It glistened with lubrication, the wetness creating a sickeningly sweet smack every time his wrist came in contact with his pelvis.

Stan trailed his gaze up Bill’s body, stopping briefly to admire the way he plucked at his nipples, and then continuing until he settled on Bill’s face.

His features were scrunched up tightly; creases formed at the edges of his eyes which were wound tightly shut, and his mouth gaped open in a silent scream.

Stan finally tore his eyes away from Bill to check the clock again, and was surprised to find that far more time has gone by than he’d thought. Bill had a bit of a habit of mesmerizing Stan, with those choked out moans and fucked out eyes, he'd pull him in until hours had gone by in seconds.

"Twenty seconds left." Stan warned, watching as Bill’s hand tripled in speed, becoming a blur of motion that Stan couldn’t keep up with. He wondered absently if Bill would be all chaffed after this, made a mental note to run Bill an aloe vera bath when they were all done.

Ten seconds left. Stan began counting aloud.

“10… 9… 8…”

“Fuck fuck fuck fuck fuck.”

“7… 6… 5…”

“Oh my god f-fuck I’m-”

“4… 3… 2…”

As if set on a timer, as soon as the clock hit its time, so did Bill.

Stan looked on in satisfaction as Bill hit his climax, watching everything in him go slack as the waves of pleasure took over. Hot stripes of cum shot across Bill’s stomach and the bed spread, as tears streaked down his ruddied cheeks. He was silent; no moans or screams or swears, just quiet release. He didn’t make a peep until the very last of his contents had been squeezed out of him, and then with a grunt he finally let himself collapse.

Stan carefully pulled out of him, immediately shucking off the defiled stiletto and following suit with his other, shortening him a good five inches. Stan wrapped his arms around Bill’s form and helped hike him up on the bed, aiding his tired muscles to get into a comfortable position. He was about to head off to the bathroom to grab his after care kit when two big arms wrapped around his waist, preventing him from moving.

Stan chuckled lowly, turning back around to face his boyfriend.

“I gotta get you cleaned up, baby.” Stan said in a hush.

“Later.” Bill resisted, nuzzling into Stan’s neck and kissing his collarbone.

Stan relented easily, not having it in him to part from Bill just yet either.

They laid there for long enough to drift off, losing consciousness to the world together. Stan would have an unpleasant mess to clean up when they awoke, but it would all be worth it. It was always worth it with Bill.

**Author's Note:**

> I got this as a request from my lovely friend Jack ages ago, but just now completed it. I know this is a little bit of a niche kink, but I'm nothing if not adventurous, just like the boys. ;)


End file.
